Monkey, Arthur Waley’s English translation of a sixteenth-century Chinese novel Xiyou ji (Journey to the West), plays an important role in the canonization of the original novel as a masterpiece of world literature. This study seeks to explore Waley’s multiple relationship with Xiyou ji and highlight various factors that contribute to the canonization of the novel in a larger space of world literature. Through examination of Waley’s personal configuration of the novel (and his following engagement with the Xiyou ji tradition), it demonstrates how Monkey becomes what Damrosch calls “the locus of a negotiation between two different cultures,” and how Waley’s engagement with the novel serves as a strategy for addressing his multi-dimensional concerns and especially the construction of the self as translator, scholar, and creative writer.